Potassium Carbonate → HCID 59603146, compound

HRID 2061364Notes

Reaction equation

HRID 2061364 reaction equation
[OH:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([O:12][CH3:13])=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:20]([O:22][CH:23]([O:26][CH2:27][CH3:28])[CH2:24]Br)[CH3:21]>CN(C=O)C>[CH2:20]([O:22][CH:23]([O:26][CH2:27][CH3:28])[CH2:24][O:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([O:12][CH3:13])=[CH:6][C:3]=1[CH:4]=[O:5])[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 71720462-hydroxy-3,5-dimethoxybenzaldehyde

Product 1

HCID 59603146HCID 59603146, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension containing 38 (1.1 g, 6.0 mmol) and K2CO3 (1.0 g, 7.2 mmol) in DMF (100 mL), bromoacetaldehyde diethyl acetal (0.93 mL, 6.0 mmol) was added dropwise. The mixture was refluxed for 4 h. After cooling, the precipitate was filtered off and the solvent was evaporated in vacuo. The crude residue was adsorbed on silica gel and purified by flash chromatography. The product was eluted with hexane/EtOAc (4:1) to give 39 (1.2 g, 67%) as an oil. 1H NMR (500 MHz, CDCl3): δ: 10.50 (1H, s, CHO), 6.88 (1H, d, J4,6=2.9 Hz, H-6), 6.74 (1H, d, J4,6=2.9 Hz, H-4), 4.83 (1H, t, J4,6=5.3 Hz, CH), 4.14 (2H, d, J4,6=5.3 Hz, CH2), 3.88 (3H, s, OMe), 3.83 (3H, s, OMe), 3.77-3.71) (2H, m, CH2CH3), 3.63-3.58 (2H, m, CH2CH3), 1.24 (6H, t, J=7.1 Hz, 2×CH3).

Workup

  1. additionwas added dropwise
  2. temperatureThe mixture was refluxed for 4 h
  3. temperatureAfter cooling
  4. filtrationthe precipitate was filtered off
  5. customthe solvent was evaporated in vacuo
  6. custompurified by flash chromatography
  7. washThe product was eluted with hexane/EtOAc (4:1)

Sources & evidence

ORD record
ord-2a89a79c2666464d81078c2ba3e4b784
Source dataset
uspto-grants-2012_10
Patent number
US08283340B2

Reaction notes

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